{1-[(tert-butoxy)carbonyl]-5-methoxy-1H-indol-2-yl}boronic acid

• ChemBase ID: 77187
• Molecular Formular: C14H18BNO5
• Molecular Mass: 291.10742
• Monoisotopic Mass: 291.12780308
• SMILES: n1(C(=O)OC(C)(C)C)c(cc2cc(ccc12)OC)B(O)O
• Canonical SMILES: COc1ccc2c(c1)cc(n2C(=O)OC(C)(C)C)B(O)O
• InChI: InChI=1S/C14H18BNO5/c1-14(2,3)21-13(17)16-11-6-5-10(20-4)7-9(11)8-12(16)15(18)19/h5-8,18-19H,1-4H3
• InChIKey: PZLVPMBCKHDVKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {1-[(tert-butoxy)carbonyl]-5-methoxy-1H-indol-2-yl}boronic acid
• IUPAC Traditional name: 1-(tert-butoxycarbonyl)-5-methoxyindol-2-ylboronic acid
• Synonyms: 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid; 1-(tert-Butoxycarbonyl)-5-methoxy-(1H-indol-2-yl)boronic acid; 5-Methoxy-1H-indole-2-boronic acid, N-BOC protected; N-(tert-Butoxycarbonyl)-5-methoxyindole-2-boronic acid; N-Boc-5-methoxyindole-2-boronic acid; N-Boc-5-methoxy-2-indolylboronic acid; 1-Boc-5-甲氧基吲哚-2-硼酸; N-(叔丁氧基羰基)-5-甲氧基吲哚-2-硼酸; N-叔丁氧基羰基-5-甲氧基-2-吲哚硼酸

Database IDs

• CAS Number: 290331-71-4
• MDL Number: MFCD04039006
• PubChem SID: 162042061; 24885571
• PubChem CID: 2794716

CALCULATED PROPERTIES

• Acid pKa: 8.225258
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4149876
• LogD (pH = 7.4): 2.3555806
• Log P: 2.4158
• Molar Refractivity: 72.106 cm^3
• Polarizability: 31.216642 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 102-107 °C; 102-108°C

Safety Information

• Storage Warning: Irritant/Light Sensitive/Keep Cold/Store under Argon
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 97%; 98%
• Empirical Formula (Hill Notation): C14H18BNO5

DETAILS

Sigma Aldrich - 680516

General description
May contain varying amounts of anhydride.
Packaging
1, 10 g in glass bottle
Application
Reactant for:
• Preparation of dihalogenated pyrazoles via dipolar cycloaddition by palladium-catalyzed cross-coupling processes1
• Suzuki-Miyaura cross-coupling2
• Synthesis of the isocryptolepine alkaloid and its related skeletons using a modified Pictet-Spengler reaction3